Medium effects on the α-effect in DMSO-H2O mixtures - Comparative studies of p-nitrophenyl benzoate and acetate - Dissection of ground-state and transition-state effects

Canadian Journal of Chemistry

Volumn 84, Issue 11, 2006, Pages 1550-1556

  Um, Ik Hwan ^a   Shin, Young Hee ^a   Han, Jeong Yoon ^a   Buncel, Erwin ^a,b  

^a Ewha Womans University   (South Korea)

^b QUEEN S UNIVERSITY   (Canada)

Author keywords

Desolvation; Ground state; Medium effect; Solvation; The effect; Transition state

Indexed keywords

DESOLVATION; SOLVATION; TRANSITION STATES;

GROUND STATE; RATE CONSTANTS; REACTION KINETICS; SOLVENTS;

ESTERS;

4 CHLOROPHENOL; 4 CHLOROPHENOXIDE; 4 NITROPHENYLACETIC ACID; 4 NITROPHENYLBENZOATE; ACETIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; BUTAN 2,3 DIONE MONOXIMATE; DIMETHYL SULFOXIDE; OXIME DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; SOLVATION; SOLVENT EFFECT;

EID: 33846999868     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-156     Document Type: Article

References (57)

1. For reviews see: (a) E. Buncel and I.H. Um. Tetrahedron, 60, 7801 (2004);
2. (b) E. Buncel and S. Hoz. Isr. J. Chem. 26, 313 (1985);
3. (c) A.P. Grekov and V.Y. Veselov. Usp. Khim. 47, 1200 (1978);
4. (d) N.J. Fina and J.O. Edwards. Int. J. Chem. Kinet. 5, 1 (1973).
5. (a) F. Terrier, E. Le Guevel, A.P. Chatrouse, G. Moutiers, and E. Buncel. Chem. Commun. (Cambridge), 600 (2003);
6. (b) E. Buncel, C. Cannes, A.P. Chatrousse, and F. Terrier. J. Am. Chem. Soc. 124, 8766 (2002);
7. (c) A.P. Moutiers, E. Le Guevel, L. Villien, and F. Terrier. J. Chem. Soc. Perkin Trans. 2, 7 (1997);
8. (d) F. Terrier, G. Moutiers, L. Xiao, E. Le Guvel, and F. Guir. J. Org. Chem. 60, 1748 (1995);
9. (e) F. Terrier, P. McCormack, E. Kizilian, J.C. Halle, P. Demerseman, F. Guir, and C. Lion. J. Chem. Soc. Perkin Trans. 2, 153 (1991);
10. (f) G. Moutiers, E. Le Guevel, C. Cannes, F. Terrier, and E. Buncel. Eur. J. Org. Chem. 17, 3279 (2001).
11. (a) C.F. Bernasconi and C. Murray. J. Am. Chem. Soc. 108, 5251 (1986);
12. (b) C.F. Bernasconi and A. Leyes. J. Am. Chem. Soc. 117, 1703 (1995);
13. (c) C.F. Bernasconi and M. Stronach. J. Org. Chem. 56, 1993 (1991);
14. (d) D. Herschlag and W. P. Jencks. J. Am. Chem. Soc. 112, 1951 (1990);
15. (e) D.J. Palling and W.P. Jencks. J. Am. Chem. Soc. 106, 4869 (1984);
16. (f) H.J. Dixon, and T.C. Bruice. J. Am. Chem. Soc. 94, 2052 (1972);
17. (g) H.J. Dixon and T.C. Bruice. J. Am. Chem. Soc. 93, 6592 (1971).
18. (a) K.R. Fountain. J. Phys. Org. Chem. 18, 481 (2005);
19. (b) K.R. Fountain, C.J. Felkerson, J.D. Driskell, and B.D. Lamp. J. Org. Chem. 68, 1810 (2003);
20. (c) K.R. Fountain, D.B. Tad-y, T.W. Paul, and M.V. Golynskiy. J. Org. Chem. 64, 6547 (1999);
21. (d) K.R. Fountain, and K.D. Patel. J. Org. Chem. 62, 4795 (1997).
22. (a) Y. Ren and H. Yamataka. Org. Lett. 8, 119 (2006);
23. (b) J.D. Evanseck, J.F. Blake, and W.L. Jorgensen. J. Am. Chem. Soc. 109, 2349 (1987);
24. (c) S. Hoz and E. Buncel. Tetrahedron Lett. 25, 3411 (1984);
25. (d) E. Buncel and S. Hoz. Tetrahedron Lett. 24, 4777 (1983);
26. (e) S. Hoz. J. Org. Chem. 47, 3545 (1982).
27. (a) C.H. DePuy, E.W. Della, J. Filley, J.J. Grabowski, and V.M. Bierbaum. J. Am. Chem. Soc. 105, 2481 (1983);
28. (b) S. Wolfe, D.J. Mitchell, and H.B. Schlegel. J. Am. Chem. Soc. 103, 7694 (1981).
29. (a) E. Buncel and I.H. Um. J. Chem. Soc. Chem. Commun. 595 (1986);
30. (b) I.H. Um and E. Buncel. J. Org. Chem. 65, 577 (2000);
31. (c) R.M. Tarkka and E. Buncel. J. Am. Chem. Soc. 117, 1503 (1995);
32. (d) i.H. Um, J.Y. Hong, and E. Buncel. Chem. Commun. (Cambridge), 27 (2001);
33. (e) I.H. Um, S.J. Hwang, and E. Buncel. J. Org. Chem. 71, 915 (2006).
34. (a) I.H. Um, Y.M. Park, and E. Buncel. Chem. Commun. (Cambridge), 1917 (2000);
35. (b) I.H. Um, E.J. Lee, and E. Buncel. J. Org. Chem. 66, 4859 (2001).
36. I.H. Um and E. Buncel. J. Am. Chem. Soc. 123, 11111 (2001).
37. (a) I.H. Um, J.S. Lee, and S.M. Yuk. J. Org. Chem. 63, 9152 (1998);
38. (b) I.H. Um, H.W. Lee, J.S. Lee, H.J. Moon, and D.S. Kwon. J. Org. Chem. 62, 5939 (1997).
39. R.A. Moss, S. Swarup, and S. Ganguli. J. Chem. Soc. Chem. Commun. 860 (1987).
40. (a) E. Buncel, R. Stairs, and H. Wilson. The role of the solvent in chemical reactions. Oxford University Press, Oxford, UK. 2003.
41. (b) E. Buncel and H. Wilson. Adv. Phys. Org. Chem. 14, 133 (1977);
42. (c) E. Buncel and H. Wilson. Acc. Chem. Res. 12, 42 (1979).
43. A.J. Parker. Chem. Rev. 69, 1 (1969).
44. C.F. Bernasconi. Adv. Phys. Org. Chem. 27, 119 (1992).
45. (a) R.D. Rogers and K.R. Seddon. Ionic liquid IIIA: fundamentals, progress, challenges, and opportunities - Properties and structure. Adv. Chem. Ser. 901, American Chemical Society, Washington D.C. 2005;
46. (b) R.D. Rogers and K.R. Seddon. Ionic liquid IIIB: fundamentals, progress, challenges, and opportunities-transformations and processes. Adv. Chem. Ser. 902, American Chemical Society, Washington D.C. 2005
47. (a) D.J. Cram. Pure Appl. Chem. 7, 155 (1963);
48. (b) E. Buncel and J.M. Dust. Carbanion chemistry. Structures and mechanisms. Oxford University Press-ACS, Oxford and Washington D.C. 2003.
49. R.A. Cox and R. Stewart. J. Am. Chem. Soc. 98, 488 (1976).
50. F.G. Bordwell. Acc. Chem. Res. 21, 456 (1988).
51. (a) E. Grunwald and S. Winstein. J. Am. Chem. Soc. 70, 846 (1948);
52. (b) T.W. Bentley and P.v.R. Schleyer. Adv. Phys. Org. Chem. 14, 1 (1977).
53. (a) D.E. Bowen, M.A. Priesand, and M.P. Eastman. J. Phys. Chem. 78, 2611 (1974);
54. (b) E.A. Symons. Can. J. Chem. 24, 3940 (1971), and refs. therein.
55. I.H. Um, S.J. Oh, and D.S. Kwon. Tetrahedron Lett. 36, 6903 (1995).
56. P. Harberfied, J. Friedman, and M.F. Pinkston. J. Am. Chem. Soc. 94, 71 (1972).
57. C.D. Ritchie. In Solute-solvent interactions. Edited by J.F. Coetzee and C.D. Ritchie. Marcel Dekker, New York. 1969.